Our Commitment

Greatest Expectations is committed to creating a culture that reflects the diversity of our clients. With that goal in mind, we understand, accept, and celebrate differences among people. We welcome everyone and do not discriminate on on the basis of race, ethnicity, age, religion, physical ability, sexual orientation, gender identity, and gender.


Behind the scenes with the Greatest Expectations Team

Greatest Expectations Events from doug mcgoldrick on Vimeo.


Heather Vickery

Chicago Wedding Planner Heather Vickery

Owner + Event Director of Greatest Expectations 

Heather’s background in event design, marketing, hotel sales, catering and non-profit event management gives her unparalleled experience in wedding and event planning. Fifteen years ago, she channeled this expertise into her own event-planning business, Greatest Expectations, which has blossomed into one of Chicago’s most celebrated event planning and design firms.

The Knot voted Heather and her team “Best of Weddings” in 2009, 2010 and 2011. For the last five years, she’s won the Couple’s Choice Award and has appeared on the exclusive Chicago Social Bride’s Luxe List. She is a Wish Grantor for Wish Upon a Wedding and was recently awarded their  prestigious Shining Star Award.

Additionally, she founded the Chicago-based eleven eleven WEDDING Giveaway in 2010, which has united dozens of event professionals to give couples the luxury weddings of their dreams, with a combined value of more than $225,000.

Heather also enjoys her involvement at the Gay Wedding Institute (GWI) as a trainer and event producer. The Gay Wedding Institute trains wedding professionals towards the mission of eliminating homophobia and heteronormative practices from the wedding industry. GWI is the world’s only wedding certification course that focuses on the LGBT Market.

Early in her career, Heather founded the American Cancer Society of Chicago’s “Young Professionals Board,” served as Director of Sports Marketing Events for Special Olympics Illinois, and coordinated the grand opening of W Hotels in Chicago.

Heather says event planning is more than a career for her – it’s a labor of love, inspired by her clients’ ideas and guided by her knowledge and expertise. She works closely with clients to plan exceptional events tailored to their unique tastes and needs, designed to come together seamlessly and beautifully. Clients praise her special ability to reduce the stress of planning a wedding while making the entire process – and the big day – a truly enjoyable and memorable experience.

Heather’s work has been featured in the following prestigious print magazines, blogs and news media sites: Chicago Social Brides, The Knot Chicago, ChicagoStyle Weddings, Get Married,  Parade Magazine, Chicago Wedding & Party Resource, Elizabeth Anne Designs, 10 Thousand Couples, Equally Wed, Style Me Pretty, Bicycle Built for Two, OneWed, Be U WeddingsWindy City Times, ABC 7, WGN, CBS.

Photo by Olivia Leigh Photographie
Make up by Nika Vaughan
Hair by Jon-David

Jennifer George

Event Manager

After many years working in theatre production where she had the unique experience of balancing dreams and vision with venue and resources, Jennifer has honed the skills of an uber planner and is thrilled to be part of the Greatest Expectations team.

Jennifer has worked for many prestigious organizations including The Goodman Theatre, the Crucible touring show (37 cities in four months!), MSGA Globe Program in London, Chicago Tribune  Lit Fest and Chicago Ideas Week.

Anticipating unforeseen obstacles and rerouting accordingly is a way of life in theater, life in general as well as with motherhood.  Jennifer’s brightest and on going production is her family comprised of her husband, their identical twin sons and super spunky daughter.


Pem Hessing

Event Coordinator

Prior to joining the Greatest Expectations team, Pem worked in New York City in retail marketing, public relations, copywriting, and brand event planning. Pem has planned events with brands and media partners such as Covergirl, Disney, Swarvoski Elements, Benefit Cosmetics, Lucky Magazine, Teen Vogue, and MTV Networks. Used to wearing multiple hats at once, Pem understands how important the ‘little details’ are and also truly enjoys them.

A graduate of Chicago’s Roosevelt University, Pem is thrilled to be back in Chicago and working with Greatest Expectations.


Kristine Fachet

Wedding Party Stylist / Attendant

Kristine brings 15 years of theatrical costuming experience to the Greatest Expectations team as a personal wedding parry stylist/attendant.  Her meticulous attention to detail and understanding of fit and fabric will ensure your wedding party is “stage-ready” and everyone is looking their very best.  She has worked as a stylist with some of Chicago’s top hair and makeup artists, and also as a alterations expert for local bridal boutiques.  Kristine’s talents reach far and wide, including her own line of custom handbags, Sur Le Feu Handbags & Accessories.


Andrew Gurschick

Event Coordinator

Andrew has over 20 years in the hospitality industry with over 15 years of management experience.  Managing over 26,000 square feet of banquet space and large city hotels has provided Andrew with a wealth of knowledge and experience. He has a talent for seeing not only the big picture but also the smallest details.

Andrew has a passion for food! Growing up he cooked, with his grandmother, from the young age of three. Weather it was being a teacher’s assistant to the first year students in his high school vocational program to getting his Associates Degree in Culinary Arts from New England Culinary Institute. Andrew brings so many amazing talents to the Greatest Expectations team.


Amber Porter

Event Coordinator

Amber came to the Greatest Expectations team with loads of theatre and production experience. She has worked in Chicago for 15 years as a stage manager, production manager, event producer and even a carpenter (these skills come in very handy onsite at weddings!).

In her “free” time she’s a bit of a crafty nerd who loves to knit, read and especially loves to get outdoors and go hiking, camping & exploring with her wonderful husband. We think it’s cool to be a nerd.


Georgia Gerber

Social Media Maven

Georgia joins the Greatest Expectations team as the heart and soul of our social media team, having spent many summers trailing behind her father as he photographed hundreds of weddings. She has worked in many different aspects of the wedding industry and knows exactly what excites and interests our clients. Georgia is a junior at DePaul University where she studies Political Science and Arabic (talk about using both sides of the brain – this girl is a total smarty-pants!). Georgia hopes to take her degree to Washington someday where she plans on working in foreign diplomacy. Until then, we are delighted to have her attention to detail and unmatched talent for social media.


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